Compound containing 5-membered heterocycles, organic light-emitting device using same, and terminal comprising the latter

ABSTRACT

Disclosed are a compound including 5-membered heterocycles, an organic electronic device using the same, and a terminal including the latter.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a compound containing 5-memberedheterocycles, an organic electronic device using the same, and aterminal including the latter.

2. Description of the Prior Art

In general, an organic light emitting phenomenon indicates conversion ofelectric energy into light energy by means of an organic material. Anorganic electronic device using the organic light emitting phenomenongenerally has a structure including an anode, a cathode, and an organicmaterial layer interposed therebetween. Herein, in many cases, theorganic material layer may have a multi-layered structure havingrespective different materials in order to improve efficiency andstability of an organic electronic device. For example, it may include ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer, and the like.

Materials used as an organic material layer in an organic electronicdevice may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, etc. according to their functions. Then, the lightemitting material may be divided into a high molecular weight type and alow molecular weight type according to their molecular weight, and maybe divided into a fluorescent material from electronic singlet excitedstates and a phosphorescent material from electronic triplet excitedstates according to their light emitting mechanism. Further, the lightemitting material can be classified into a blue, green or red lightemitting material and a yellow or orange light emitting materialrequired for giving a more natural color, according to a light emittingcolor.

Meanwhile, when only one material is used as a light emitting material,an efficiency of a device is lowered owing to a maximum luminescencewavelength being moved to a longer wavelength due to the interactionbetween the molecules, the deterioration of color purity and thereduction in light emitting efficiency. Therefore, a host/dopant systemcan be used as the light emitting material for the purpose of enhancingthe color purity and the light emitting efficiency through energytransfer. It is based on the principle that if a small amount of adopant having a smaller energy band gap than a host forming a lightemitting layer is mixed with the light emitting layer, excitons whichare generated in the light emitting layer are transported to the dopant,thus emitting a light having a high efficiency. Here, since thewavelength of the host is moved according to the wavelength of thedopant, a light having a desired wavelength can be obtained accordingthe kind of the dopant.

In order to allow the organic electronic device to fully exhibit theabove-mentioned excellent characteristics, a material constituting theorganic material layer in the device, for example, a hole injectionmaterial, a hole transport material, a light emitting material, anelectron transport material and an electron injection material should beessentially composed of a stable and efficient material. However, thedevelopment of a stable and efficient organic material layer materialfor the organic electronic device has not yet been fully realized.Accordingly, the development of new materials is continuously desired.

SUMMARY OF THE INVENTION

In order to solve the above-mentioned problems occurring in the priorart, the inventors of the present invention found that when anovel-structural compound including three or more 5-memberedheterocycles is employed in an organic electronic device, it is possibleto significantly improve luminous efficiency, stability, and a life spanof the device.

Accordingly, an object of the present invention is to provide a novelcompound containing 5-membered heterocycles, an organic electronicdevice using the same, and a terminal including the latter.

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

In accordance with another aspect of the present invention, there isprovided a compound represented by Formula below.

The inventive novel-structural compound including three or more5-membered heterocycles may be used as a hole injection material, a holetransport material, a light emitting material, and/or an electrontransport material appropriate for a fluorescent or phosphorescentdevice of all colors (such as red, green, blue, white, etc.), and isuseful as a host material for various colors of a phosphorescent dopant.

Also, the present invention provides an organic electronic deviceincluding the compound represented by Formula above, and a terminalincluding the organic electronic device.

According to an embodiment of the present invention, the compoundincluding three or more 5-membered heterocycles can perform variousroles in an organic electronic device and a terminal thereof.Especially, it is useful as a hole injection material, a hole transportmaterial, a light emitting material, and/or an electron transportmaterial appropriate for a fluorescent or phosphorescent device of allcolors (such as red, green, blue, white, etc.), and preferably useful asa host material for various colors of a phosphorescent dopant.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other objects, features and advantages of the presentinvention will be more apparent from the following detailed descriptiontaken in conjunction with the accompanying drawings, in which:

FIGS. 1 to 6 show examples of an organic electro-luminescence devicewhich can employ a compound according to the present invention.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, exemplary embodiments of the present invention will bedescribed with reference to the accompanying drawings. In the followingdescription, the same elements will be designated by the same referencenumerals although they are shown in different drawings. Further, in thefollowing description of the present invention, a detailed descriptionof known functions and configurations incorporated herein will beomitted when it may make the subject matter of the present inventionrather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

The present invention provides a compound represented by Formula 1below.

in Formula 1,

(1) R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁ and R₁₂ each areindependently selected from the group consisting of a hydrogen atom, ahalogen atom, a cyano group, an alkoxy group, a thiol group, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkenyl group having 1 to 50 carbon atoms,a substituted or unsubstituted arylene group having 5 to 60 carbonatoms, a substituted or unsubstituted aryl group having 5 to 60 carbonatoms, a substituted or unsubstituted aryloxy group having 5 to 60carbon atoms, a substituted or unsubstituted C₁˜C₅₀ alkyl group havingat least one of sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) andsilicon (Si), a substituted or unsubstituted C₅˜C₆₀ heteroaryl grouphaving at least one of sulfur (S), nitrogen (N), oxygen(O), phosphorous(P) and silicon (Si), and a substituted or unsubstituted C₅˜C₆₀heteroaryloxy group having at least one of sulfur, nitrogen, oxygen,phosphorous and silicon.

(2) R₁₃ and R₁₄ each are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedalkenyl group having 1 to 50 carbon atoms, a substituted orunsubstituted arylene group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryl group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 60 carbon atoms, asubstituted or unsubstituted C₁˜C₅₀ alkyl group having at least one ofsulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur, nitrogen, oxygen, phosphorous andsilicon.

(3) X may include carbon (CRaRb), nitrogen (NRc), oxygen (O),phosphorous (PRd), sulfur (S), silicon (SiReRf) or germanium (GeRgRh),wherein Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh each are independentlyselected from the group including an alkyl group having 1 to 50 carbonatoms, and an aryl group having 6 to 60 carbon atoms.

(4) R₁ and R₂, R₃ and R₄, R₄ and R₅, R₅ and R₆, R₇ and R₈, R₈ and R₉, R₉and R₁₀, and R₁₁ and R₁₂ may form a saturated or unsaturated cyclic ringtogether with an adjacent group.

(5) R₂ and R₁₃, and R₁₁ and R₁₄ may form a saturated or unsaturatedcyclic ring together with an adjacent group.

(6) The compound represented by Formula 1 may have a symmetric orasymmetric structure with respect to X.

(7) The compound having the structural formula represented by Formula 1may be used in a soluble process.

Also, in another aspect, the present invention provides a compoundrepresented by Formula 2.

(1) R₁, R₂, R₁₁ and R₁₂ each are independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a cyano group, an alkoxygroup, a thiol group, a substituted or unsubstituted alkyl group having1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having1 to 50 carbon atoms, a substituted or unsubstituted alkenyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted arylenegroup having 5 to 60 carbon atoms, a substituted or unsubstituted arylgroup having 5 to 60 carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 60 carbon atoms, a substituted orunsubstituted C₁˜C₅₀ alkyl group having at least one of Sulfur (S),nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), a substitutedor unsubstituted C₅˜C₆₀ heteroaryl group having at least one of sulfur(S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), and asubstituted or unsubstituted C₅˜C₆₀ heteroaryloxy group having at leastone of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si).

(2) R₁₃ and R₁₄ each are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedalkenyl group having 1 to 50 carbon atoms, a substituted orunsubstituted arylene group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryl group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 60 carbon atoms, asubstituted or unsubstituted C₁˜C₅₀ alkyl group having at least one ofsulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C⁵˜C₆₀ heteroaryloxy grouphaving at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorous(P) and silicon (Si).

(3) R₁₅, R₁₆, R₁₇ and R₁₈ each are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted arylgroup having 5 to 60 carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 60 carbon atoms, a substituted orunsubstituted C₁˜C₅₀ alkyl group having at least one of sulfur (S),nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorous(P) and silicon (Si).

(4) X may include carbon (CRaRb), nitrogen (NRc), oxygen (O),phosphorous (PRd), sulfur (S), silicon (SiReRf) or germanium (GeRgRh),wherein Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh each are independentlyselected from the group including an alkyl group having 1 to 50 carbonatoms, and an aryl group having 6 to 60 carbon atoms.

(5) R₁ and R₂, and R₁₁ and R₁₂ may form a saturated or unsaturatedcyclic ring together with an adjacent group.

(6) The compound having the structural formula represented by Formula 2may be used in a soluble process.

According to one embodiment of the present invention, specific examplesof a compound including three or more 5-membered heterocycles,represented by Formula 1 or 2, may include compounds represented byFormula 3. However, the present invention is not limited thereto.

There exist various organic electronic devices which employ compoundsincluding three or more 5-membered heterocycles, as described withreference to Formulas 1 to 3, as an organic material layer. The organicelectronic devices in which compounds including three or more 5-memberedheterocycles, as described with reference to Formulas 1 to 3, can beemployed, may include, for example, an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC) drum, anorganic transistor (organic TFT), a photodiode, an organic laser, alaser diode, and the like.

As one example of the organic electronic devices in which compoundsincluding three or more 5-membered heterocycles, as described withreference to Formulas 1 to 3, can be used, an organic light emittingdiode (OLED) will be described below, but the present invention is notlimited thereto. The above described compound including three or more5-membered. heterocycles may be applied to various organic electronicdevices.

In another embodiment of the present invention, there is provided anorganic electronic device (organic electro-luminescence device)including a first electrode, a second electrode, and an organic materiallayer interposed between these electrodes, in which at least one oforganic material layers includes the compounds represented by Formulas 1to 3.

FIGS. 1 to 6 show examples of an organic electro-luminescence devicewhich can employ a compound according to the present invention.

The organic electro-luminescence device according to another embodimentof the present invention may be manufactured by means of a manufacturingmethod and materials conventionally known in the art in such a mannerthat it can have a conventionally known structure, except that at leastone of organic material layers including a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer,and an electron injection layer is formed in such a manner that it caninclude the compounds represented by Formulas 1 to 3.

The structures of the organic electro-luminescence device according toanother embodiment of the present invention are shown in FIGS. 1 to 6,but the present invention is not limited to the structures. Herein, thereference numeral 101 indicates a substrate, 102 indicates an anode, 103indicates a hole injection layer (HIL), 104 indicates a hole transportlayer (HTL), 105 indicates a light emitting layer (EML), 106 indicatesan electron injection layer (EIL), 107 indicates an electron transportlayer (ETL), and 108 indicates a cathode. Although not shown, such anorganic electro-luminescence device may further include a hole blockinglayer (HBL) for blocking movement of holes, an electron blocking layer(EBL) for blocking movement of electrons, and a protective layer. Theprotective layer may be formed in such a manner that it, as an uppermostlayer, can protect an organic material layer or a cathode.

Herein, the compound including three or more 5-membered heterocycles, asdescribed with reference to Formulas 1 to 3, may be included in at leastone of organic material layers including a hole injection layer, a holetransport layer, a light emitting layer, and an electron transportlayer. Specifically, the compound including three or more 5-memberedheterocycles, as described with reference to Formulas 1 to 3, may besubstituted for at least one of a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, an electroninjection layer, a hole blocking layer, an electron blocking layer, anda protective layer, or may be used in combination with these layers. Ofcourse, the compound may be used for not only one layer of the organicmaterial layers but also two or more layers.

Especially, the compound including three or more 5-memberedheterocycles, as described with reference to Formulas 1 to 3, may beused as a hole injection material, a hole transport material, a lightemitting material, and/or an electron transport material appropriate fora fluorescent or phosphorescent device of all colors (such as red,green, blue, white, etc.), and especially is useful as a greenphosphorescent host material.

For example, in manufacturing of the organic electro-luminescence deviceaccording to another embodiment of the present invention, a metal, aconductive metal oxide, or an alloy thereof is deposited on a substrateby means of PVD (physical vapor deposition) such as sputtering or e-beamevaporation so as to form an anode, and then an organic material layerincluding a hole injection layer, a hole transport layer, a lightemitting layer, an electron transport layer, and an electron injectionlayer is formed thereon, and a material used as a cathode is depositedthereon.

Besides, on a substrate, a cathode material, an organic material layer,and an anode material may be sequentially deposited so as to provide anorganic electronic device. The organic material layer may be formed in amulti-layered structure including a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer,and an electron injection layer, but the present invention is notlimited thereto. It may be formed in a single layer structure. Further,the organic material layer may be manufactured with a smaller number oflayers by using various polymer materials by means of a solvent process(e.g., spin coating, dip coating, doctor blading, screen printing,inkjet printing, or thermal transfer) instead of deposition.

In the organic electro-luminescence device according to anotherembodiment of the present invention, the organic material layer (e.g., alight emitting layer) may be formed by a soluble process of the abovedescribed compound including three or more 5-membered heterocycles.

The substrate is a support for the organic electro-luminescence device,and may employ a silicon wafer, a quartz or glass plate, a metallicplate, a plastic film or sheet.

On the substrate, an anode is positioned. Such an anode allows holes tobe injected into a hole injection layer positioned thereon. As an anodematerial, a material having a high work function is preferably used sothat injection of holes into an organic material layer can be smoothlycarried out. Specific examples of an anode material used for the presentinvention may include: metals (such as vanadium, chromium, copper, zinc,gold) or alloys thereof; metallic oxides such as zinc oxide, indiumoxide, indium tin oxide (ITO), indium zinc oxide (IZO); a metal-oxidecombination such as ZnO:Al or SnO₂:Sb; and conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophenel](PEDT), polypyrrole and polyaniline, but the present invention is notlimited thereto.

On the anode, a hole injection layer is positioned. A material for sucha hole injection layer is required to have a high efficiency forinjecting holes from an anode, and to be able to efficiently transportthe injected holes. For this, the material has a low ionizationpotential, a high transparency against visible light, and a highstability for holes.

As a hole injection material, a material into which holes can be wellinjected from an anode at a low voltage is used. Preferably, HOMO(highest occupied molecular orbital) of the hole injection materialranges from a work function of an anode material to HOMO of adjacentorganic material layers. Specific examples of the hole injectionmaterial may include metal porphyrine-, oligothiophene-, andarylamine-based organic materials, hexanitrile hexaazatriphenylene- andquinacridone-based organic materials, perylene-based organic materials,and anthraquinone-, polyaniline-, and polythiophene-based conductivepolymers, but the present invention is not limited thereto.

On the hole injection layer, a hole transport layer is positioned. Sucha hole transport layer receives holes transferred from the holeinjection layer and transfers them to an organic light emitting layerpositioned thereon. Further, the hole transport layer has a high holemobility and a high hole stability and performs a role of blockingelectrons. Besides these general requirements, it requiresheat-resistance against a device when applied to an automobile display,and thus is preferably made of a material having a glass transitiontemperature (Tg) of 70° C. or more. The examples of a materialsatisfying these conditions may include NPD (or NPB),Spiro-arylamine-based compound, perylene-arylamine-based compound,azacycloheptatriene compound, bis(diphenylvinylphenyl)anthracene,silicongermaniumoxide compound, silicon-based arylamine compound, andthe like.

On the hole transport layer, an organic light emitting layer ispositioned. Such an organic light emitting layer is made of a materialhaving a high quantum efficiency, in which holes and electrons which areinjected from an anode and a cathode, respectively, are recombined so asto emit light. As a light emitting material, a material allowing holesand electrons transferred from a hole transport layer and an electrontransport layer, respectively, to be combined so as to emit visiblelight is used. Preferably, a material having a high quantum efficiencyagainst fluorescence or phosphorescence is used.

As a material or a compound satisfying these conditions, for a greencolor, Alq3 may be used, and for a blue color, Balq(8-hydroxyquinolineberyllium salt), DPVBi(4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl)based material, Spiro material,spiro-DPVBi(Spiro-4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl),LiPBO(2-(2-benzoxazoyl)-phenol lithium salt),bis(diphenylvinylphenylvinyl)benzene, aluminum-quinoline metal complex,imidazole, thiazol and oxazole-metal complex, or the like may be used.In order to improve the luminous efficiency of a blue color, perylene,andBczVBi(3,3′[(1,1′-biphenyl)-4,4′-diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole;DSA(distrylamine)) may be doped in a small amount. For a red color, agreen light emitting material may be doped withDCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene]-propanedinitrile)in a small amount. When a process such as inkjet printing, roll coating,spin coating, is used to form a light emitting layer,polyphenylenevinylene (PPV)-based polymer or poly fluorene may be usedfor an organic light emitting layer.

On the organic light emitting layer, an electron transport layer ispositioned. Such an electron transport layer requires a material whichhas a high efficiency for electrons injected from a cathode positionedthereon, and can efficiently transport the injected electrons. For this,a material having a high electron affinity, a high electron mobility,and a high electron stability is required. The examples of an electrontransport material satisfying these conditions may include Al complex of8-hydroxyquinoline; complex including Alq₃; organic radical compound;and hydroxyflavone-metal complex, but the present invention is notlimited thereto.

On the electron transport layer, an electron injection layer is layered.The electron injection layer may be manufactured by using a metalcomplex compound (such as Balq, Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD,spiro-PBD, TPBI, and Tf-6P) or a low molecular material including anaromatic compound having an imidazole ring or a boron compound. Herein,the electron injection layer may be formed in a thickness range of 100 Åto 300 Å.

On the electron injection layer, a cathode is positioned. Such a cathodeperforms a role of injecting electrons into the electron injectionlayer. As a material for the cathode, the same material as that used foran anode may be used. In order to achieve efficient electron injection,a metal having a low work function is more preferable. Especially,metals such as tin, magnesium, indium, calcium, sodium, lithium,aluminum, silver, or alloys thereof may be used. Further, adouble-layered electrode (e.g., lithiumfluoride and aluminum, lithiumoxide and aluminum, and strontium oxide and aluminum) with a thicknessof 1000 μm or less may be used.

As described above, the compound including three or more 5-memberedheterocycles, as described with reference to Formulas 1 to 3, may beused as a hole injection material, a hole transport material, a lightemitting material, an electron transport material and/or an electroninjection material appropriate for a fluorescent or phosphorescentdevice of all colors (such as red, green, blue, white, etc.), and may beused as a host material for various colors of a phosphorescent dopant.

The organic electro-luminescence device according to the presentinvention may be manufactured in a front luminescent type, a rearluminescent type, or a both-side luminescent type according to itsmaterials.

Meanwhile, the present invention provides a terminal which includes adisplay device and a control part for driving the display device, thedisplay device including the above described organic electronic device.The terminal means a wired/wireless communication terminal which iscurrently used or will be used in the future. The above describedterminal according to the present invention may be a mobilecommunication terminal such as a cellular phone, and may include allkinds of terminals such as a PDA, an electronic dictionary, a PMP, aremote control, a navigation unit, a game player, various kinds of TVs,and various kind's of computers.

EXAMPLE

Hereinafter, the present invention will be described more specificallywith reference to Preparation Examples and Experimental Examples.However, the following examples are only for illustrative purposes andare not intended to limit the scope of the invention.

Preparation Example

Hereinafter, Preparation Examples or Synthesis Examples of the compoundsincluding three or more 5-membered heterocycles, represented by Formula3, will be described. However, since there are many compounds includingthree or more 5-membered heterocycles, represented by Formula 3, onecompound or two compounds from among the compounds will be exemplified.A person skilled in the art of the invention should realize that othercompounds including three or more 5-membered heterocycles can beprepared through Preparation Examples as described below although theyare not exemplified.

step 1) Synthesis of Intermediate A

In a 250 mL round-bottom flask, N,N,N′,N′-Tetramethylenediamine (TMEDA)was dissolved in anhydrous Hexane. At 0° C., n-BuLi (1.6 M in hexane)was slowly added thereto for 30 minutes, and the mixture was stirred for30 minutes at room temperature. Dibenzothiophene diluted with Hexane wasadded thereto, and the resultant product was stirred at 60° C. for 2hours. Then, the temperature of the product was lowered to −70° C., andchlorotrimethylsilane was added thereto, followed by stirring for 1hour. After the completion of the reaction, the resultant product wasextracted with Hexane, and washed with water. From the extract, a smallamount of water was removed by MgSO₄ (anhydrous), followed byvacuum-filtration. Then, the product obtained after concentration of anorganic solvent was purified by column chromatography (solvent: Pentane)to give a required intermediate A (yield: 30%).

step 2) Synthesis of Intermediate B

The intermediate A obtained from the step 1) was dissolved in Carbontetrachloride. The temperature of the resultant product was lowered to−15° C., and Bromine was slowly added thereto. Then, the resultantproduct was stirred at 0° C. for 1 hour, and water was added thereto toquench the reaction. The organic layer was washed with Brine. AnhydrousMgSO₄ was used to remove water within the resultant product. Aftervacuum-filtration, the product obtained by concentration of an organicsolvent was purified by column chromatography to give a requiredintermediate B (yield: 89%).

step 3) Synthesis of Intermediate C

The intermediate B obtained from the step 2) was dissolved in anhydrousTHF. The temperature of the resultant product was lowered to −78° C.,and n-BuLi (1.6 M in Hexane) was slowly added thereto. Then, theresultant product was stirred at 0° C. for 1 hour. Then, the temperatureof the resultant product was lowered to −78° C., and Trimethyl boratewas added thereto, followed by stirring at room temperature for 12hours. After the completion of the reaction, the resultant product wasadded with 2N HCl aqueous solution, stirred for 30 minutes, andextracted with Ether. From the extract, a small amount of water wasremoved by anhydrous MgSO₄, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required intermediate C (yield: 70%).

step 4) Synthesis of Intermediate D

The intermediate C obtained from the step 3), Pd(PPh₃)₄, and K₂CO₃ weredissolved in anhydrous THF and a small amount of water, followed byreflux for 24 hours. After the completion of the reaction, the resultantproduct was cooled to room temperature, extracted with CH₂Cl₂, andwashed with water. From the extract, a small amount of water was removedby anhydrous MgSO₄, followed by vacuum-filtration. Then, the productobtained after concentration of an organic solvent was purified bycolumn chromatography to give a required intermediate D (yield: 77%).

Step 5) Synthesis of Intermediate E

The intermediate D obtained from the step 4) and triphenylphosphine weredissolved in o-dichlorobenzene, followed by reflux for 24 hours. Afterthe completion of the reaction, the solvent was removed by vacuumdistillation. Then, the concentrated product was purified by columnchromatography to give a required intermediate E (yield: 57%).

Synthesis Example 1: Synthesis of Compound 1

The intermediate E synthesized from the step 5), Iodobenzene, Pd₂(dba)₃,P(^(t)Bu)₃ and NaO^(t)Bu were dissolved in Toluene solvent, followed bystirring at 110° C. for 6 hours. After the completion of the reaction,the resultant product was cooled to room temperature, extracted withCH₂Cl₂, and washed with water. From the extract, a small amount of waterwas removed by anhydrous MgSO₄, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required compound 1 (yield: 65%).

Synthesis Example 2: Synthesis of Compound 10

The intermediate E synthesized from the step 5) was dissolved inanhydrous THF. The temperature of the resultant product was lowered to−78° C., and n-BuLi (1.6 M in Hexane) was slowly added thereto. Then,the resultant product was stirred at 0° C. for 1 hour. Then, thetemperature of the resultant product was lowered to −78° C., and2-Chloro-4,6-diphenylpyrimidine dissolved in anhydrous THF was slowlyadded thereto, followed by stirring at 60° C. for 12 hours. After thecompletion of the reaction, the resultant product was cooled to roomtemperature, extracted with CH₂Cl₂, and washed with water. From theextract, a small amount of water was removed by anhydrous MgSO₄,followed by vacuum-filtration. Then, the product obtained afterconcentration of an organic solvent was purified by columnchromatography to give a required compound 10 (yield: 48%).

Step 6) Synthesis of Intermediate F

The compound 1 obtained from Synthesis Example 1, NBS(N-bromosuccinimide), and BPO (benzoyl peroxide) were dissolved inCH₂Cl₂, followed by stirring at room temperature for 6 hours. After thecompletion of the reaction, the resultant product was added with asodium bicarbonate aqueous solution, stirred for 30 minutes, andextracted with CH₂Cl₂. Anhydrous MgSO₄ was used to remove water withinthe resultant product. After vacuum-filtration, the product obtained byconcentration of an organic solvent was purified by columnchromatography to give a required intermediate F (yield: 77%).

Synthesis Example 3: Synthesis of Compound 27

The intermediate F obtained from the step 6),4-(1-Phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid, Pd(PPh₃)₄, andK₂CO₃ were dissolved in anhydrous THF and a small amount of water,followed by reflux for 24 hours. After the completion of the reaction,the resultant product was cooled to room temperature, extracted withCH₂Cl₂, and washed with water. From the extract, a small amount of waterwas removed by anhydrous MgSO₄, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required compound 27 (yield: 57%).

Synthesis Example 4: Synthesis of Compound 58

The intermediate F obtained from the step 6), diphenylamine, Pd₂(dba)₃,P(tBu)₃ and NaO^(t)Bu were dissolved in Toluene solvent, followed bystirring at 110° C. for 9 hours. After the completion of the reaction,the resultant product was cooled to room temperature, extracted withCH₂Cl₂, and washed with water. From the extract, a small amount of waterwas removed by anhydrous MgSO₄, followed by vacuum-filtration. Then, theproduct obtained after concentration of an organic solvent was purifiedby column chromatography to give a required compound 58 (yield: 60%).

Fabrication Test of Organic Electro-Luminescence Device

An organic electro-luminescence device was manufactured according to aconventional method by using each of compounds 1, 10, 27, and 58obtained by synthesis as a light emitting host material for a lightemitting layer. First, on an ITO layer (anode) formed on a glasssubstrate, a copper phthalocyanine (hereinafter, referred to as CuPc)film as a hole injection layer was vacuum-deposited with a thickness of10 nm.

Then, on this film, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(hereinafter, referred to as a-NPD) as a hole transport compound wasvacuum-deposited with a thickness of 30 nm so as to form a holetransport layer. After the hole transport layer was formed, each of thecompounds 1, 10, 27 and 58 as a phosphorescence host material wasdeposited on the hole transport layer so as to form a light emittinglayer.

At the same time, as a phosphorescent Ir metal complex dopant,tris(2-phenylpyridine)iridium (hereinafter, referred to as Ir(ppy)₃) wasadded. Herein, in the light emitting layer, the concentration ofIr(ppy)₃ was 5 wt %. As a hole blocking layer,(1,1-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, referred to as BAlq) was vacuum-deposited with a thicknessof 10 nm, and then as an electron injection layer,tris(8-quinolinol)aluminum (hereinafter, referred to as Alq₃) wasfilm-formed with a thickness of 40 nm. Then, LiF (alkali-metal halide)was deposited with a thickness of 0.2 nm, and Al was deposited with athickness of 150 nm. The Al/LiF was used as a cathode while the organicelectro-luminescence device was fabricated.

Comparison Example 1

For comparison, instead of the inventive compound, a compound(hereinafter, referred to as CBP) represented by Formula 4 was used as alight emitting host material so as to fabricate an organicelectro-luminescence device with the same structure as that of TestExample.

TABLE 1 chro- lumi- matic- Host nous ity material of current effi- co-light Volt- density lumi- cien- ordi- emitting age (mA/ nance cy nateslayer (V) cm²) (cd/m²) (cd/A) (x, y) Example 1 compound 1 5.8 0.31 10745.3 (0.30, 0.60) Example 2 compound 5.6 0.33 105 52.2 (0.32, 10 0.61)Example 3 compound 5.6 0.31 107 50.3 (0.30, 27 0.60) Example 4 compound5.0 0.31 107 38.3 (0.30, 58 0.60) Comparative CBP 6.1 0.31 101 32.6(0.33, Example 1 0.61)

From the results noted in Table 1, it can be seen that in an organicelectro-luminescence device using the inventive material for the organicelectro-luminescence device, it is possible to obtain long-life greenlight with a high efficiency, and an improved color purity. Thus, theinventive material as a green phosphorescence host material for anorganic electro-luminescence device can significantly improve theluminous efficiency and life span.

It is natural that even though the inventive compounds are applied toother organic material layers of an organic electro-luminescence device,e.g., an electron injection layer, an electron transport layer, a holeinjection layer and a hole transport layer as well as a light emittinglayer, it is possible to achieve the same effects.

Although a preferred embodiment of the present invention has beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentsdisclosed in the present invention are intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims in such a manner that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C.§119(a) of Korean Patent Application No. 10-2009-0073915, filed on Aug.11, 2009, which is hereby incorporated by reference for all purposes asif fully set forth herein. Further, this application claims the benefitof priority in other countries than U.S., which are hereby incorporatedby reference herein.

1. A compound represented by Formula below

wherein (1) R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁ and R₁₂ eachare independently selected from the group consisting of a hydrogen atom,a halogen atom, a cyano group, an alkoxy group, a thiol group, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkenyl group having 1 to 50 carbon atoms,a substituted or unsubstituted arylene group having 5 to 60 carbonatoms, a substituted or unsubstituted aryl group having 5 to 60 carbonatoms, a substituted or unsubstituted aryloxy group having 5 to 60carbon atoms, a substituted or unsubstituted C₁˜C₅₀ alkyl group havingat least one of sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) andsilicon (Si), a substituted or unsubstituted C₅˜C₆₀ heteroaryl grouphaving at least one of sulfur (S), nitrogen (N), oxygen(O), phosphorous(P) and silicon (Si), and a substituted or unsubstituted C₅˜C₆₀heteroaryloxy group having at least one of sulfur, nitrogen, oxygen,phosphorous and silicon; (2) R₁₃ and R₁₄ each are independently selectedfrom the group consisting of a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted orunsubstituted alkenyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted arylene group having 5 to 60 carbon atoms, asubstituted or unsubstituted aryl group having 5 to 60 carbon atoms, asubstituted or unsubstituted aryloxy group having 5 to 60 carbon atoms,a substituted or unsubstituted C₁˜C₅₀ alkyl group having at least one ofsulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur, nitrogen, oxygen, phosphorous andsilicon; and (3) X comprises carbon (CRaRb), nitrogen (NRc), oxygen (O),phosphorous (PRd), sulfur (S), silicon (SiReRf) or germanium (GeRgRh),wherein Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh each are independentlyselected from the group including an alkyl group having 1 to 50 carbonatoms, and an aryl group having 6 to 60 carbon atoms.
 2. The compound asclaimed in claim 1, wherein R₁ and R₂, R₃ and R₄, R₄ and R₅, R₅ and R₆,R₇ and R₈, R₈ and R₉, R₉ and R₁₀, and R₁₁ and R₁₂ form a saturated orunsaturated cyclic ring together with an adjacent group.
 3. The compoundas claimed in claim 1, wherein R₂ and R₁₃, and R₁₁ and R₁₄ form asaturated or unsaturated cyclic ring together with an adjacent group. 4.The compound as claimed in claim 1, having a symmetric or asymmetricstructure with respect to X.
 5. A compound represented by Formula below

wherein (1) R₁, R₂, R₁₁ and R₁₂ each are independently selected from thegroup consisting of a hydrogen atom, a halogen atom, a cyano group, analkoxy group, a thiol group, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted alkenylgroup having 1 to 50 carbon atoms, a substituted or unsubstitutedarylene group having 5 to 60 carbon atoms, a substituted orunsubstituted aryl group having 5 to 60 carbon atoms, a substituted orunsubstituted aryloxy group having 5 to 60 carbon atoms, a substitutedor unsubstituted C₁˜C₅₀ alkyl group having at least one of sulfur (S),nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), a substitutedor unsubstituted C₅˜C₆₀ heteroaryl group having at least one of sulfur(S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), and asubstituted or unsubstituted C₅˜C₆₀ heteroaryloxy group having at leastone of sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si); (2) R₁₃ and R₁₄ each are independently selected from the groupconsisting of a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedalkenyl group having 1 to 50 carbon atoms, a substituted orunsubstituted arylene group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryl group having 5 to 60 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 60 carbon atoms, asubstituted or unsubstituted C₁˜C₅₀ alkyl group having at least one ofsulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen(O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorous(P) and silicon (Si); (3) R₁₅, R₁₆, R₁₇ and R₁₈ each are independentlyselected from the group consisting of a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted aryl group having 5 to 60 carbon atoms, a substituted orunsubstituted aryloxy group having 5 to 60 carbon atoms, a substitutedor unsubstituted C₁˜C₅₀ alkyl group having at least one of sulfur (S),nitrogen (N), oxygen (O), phosphorous (P) and silicon (Si), asubstituted or unsubstituted C₅˜C₆₀ heteroaryl group having at least oneof sulfur (S), nitrogen (N), oxygen (O), phosphorous (P) and silicon(Si), and a substituted or unsubstituted C₅˜C₆₀ heteroaryloxy grouphaving at least one of sulfur (S), nitrogen (N), oxygen (O), phosphorous(P) and silicon (Si); and (4) X comprises carbon (CRaRb), nitrogen(NRc), oxygen (O), phosphorous (PRd), sulfur (S), silicon (SiReRf) orgermanium (GeRgRh), wherein Ra, Rb, Rc, Rd, Re, Rf, Rg and Rh each areindependently selected from the group including an alkyl group having 1to 50 carbon atoms, and an aryl group having 6 to 60 carbon atoms. 6.The compound as claimed in claim 5, wherein R₁ and R₂, and R₁₁ and R₁₂form a saturated or unsaturated cyclic ring together with an adjacentgroup.
 7. An organic electronic device comprising one or more organicmaterial layers comprising the compound as claimed in claim
 1. 8. Theorganic electronic device as claimed in claim 7, wherein the organicmaterial layers are formed by a soluble process of the compound.
 9. Theorganic electronic device as claimed in claim 7, wherein the organicelectronic device is an organic electro-luminescence device in which afirst electrode, said one or more organic material layers, and a secondelectrode are sequentially layered.
 10. The organic electronic device asclaimed in claim 9, wherein the organic material layers comprise any oneof a hole injection layer, a hole transport layer, a light emittinglayer, an electron transport layer, and an electron injection layer. 11.The organic electronic device as claimed in claim 7, wherein the organicmaterial layers comprise a light emitting layer, and in the lightemitting layer, the compound is used as a host material.
 12. A terminalcomprising a display device and a control part for driving the displaydevice, the display device comprising the organic electronic device asclaimed in claim
 7. 13. The terminal as claimed in claim 12, wherein theorganic electronic device is any one of an organic light-emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC) drum, anorganic transistor (organic TFT), a photodiode, an organic laser, and alaser diode.